Journal of Organic Chemistry p. 4537 - 4543 (1991)
Update date:2022-08-03
Topics:
Becker, D.
Nagler, M.
Sahali, Y.
Haddad, N.
The intramolecular <2+2> photocycloaddition mechanism of alkenes tethered by a three-methylene chain to cyclohexenones has been studied.It was found that the reversion from a 1,4-diradical intermediate to starting material is slow relative to the rate of photoadduct formation.Only "straight" closure was observed in the systems studied.For compounds 1-3 and 5, the assumption that the first bond is formed between the β-carbon of the enone and C-4' leading to a 1,4-diradical is supported.For the formation of compounds 6-11, possible mechanisms are discussed.
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